With their anniversary holiday looming, Dean loses his temper when his wife forces him into bringing her little brother with them. But when Dean catches Bailey on the bed of their hotel room in a pair of his wife's silk panties, something is triggered in him. One night, after drinking too much, Dean sneaks into Bailey's room with some pretty underwear, and things take a turn that the happy husband may never come back from. It turns out that feminizing his wife's little brother may be the most thrilling thing he has ever done…